So if it's 1991 all over again, does that make Newsom Frank Jordan? DeLeon's not mean enough to float that comparison. But clearly the surprise of the mayor's race is how vulnerable a candidate Newsom is turning out to be. Right now, though, they all look a little like Frank Jordan: flawed candidates who, even if they win, won't win, exactly; it's more like they'll be the only one standing when the others lose. The question hovering above the race is who can be trusted to run this troubled "city of greatness," in DeLeon's formulation. I change my mind every day, and I'm sure I'm not alone.

Listening to Brown's last big speech in the majestic City Hall rotunda -- which the mayor restored either as a great gift to the people of San Francisco, according to his backers, or as a $300 million monument to himself, in the eyes of detractors, who used to call it the "Taj Ma Willie" -- it was hard not to notice that a political era was passing, but a new one hasn't yet dawned. It's a little bit dark politically in San Francisco right now.

Love him or hate him, Brown rescued the city from the Lilliputians of local government in 1995, uniting a coalition of labor and downtown business, blacks, gays and Asians, neighborhoods and developers. Then he ran San Francisco the only way he knew how: imperially, with a populist twist, as a last hurrah for a certain kind of old-time municipal machine. He knocked heads to end planning gridlock and pushed through stalled development projects. The rich got richer, including some of his friends, but he shared the wealth for a while by expanding the city's payroll and presiding over the great dot-com boom.

He'll be remembered for presiding over that boom -- and bust -- and for unapologetically backing pro-development policies that awakened the slumbering left four years ago. His most important legacy may be remaking the waterfront, yet the gorgeous Embarcadero rings a still-troubled downtown, where sad, sick homeless folks and sometimes-menacing panhandlers run rampant. Still, even though I've criticized Brown over the years, I find myself thinking this fractured city is going to miss his hand on the rudder, not to mention his role in pulling together our warring tribes with his charisma and singular racial appeal. Once his coalition united blacks and Asians; now they're squabbling bitterly. The ugliest battle in the city isn't the mayor's race but the fight over how students are assigned to public schools -- specifically whether school assignments should promote diversity by sending kids to far-off neighborhoods, or favor kids who live close to their schools. And school-board Greens are joining Chinese parents, many of whom are conservative, who are angry at having to send their kids across town to integrate academically weak black-and-Latino-dominated schools, in trying to topple the imperious but capable African-American superintendent, Arlene Ackerman. Ackerman is backed by Brown, but it's not clear even Brown can save her.

The mayor's State of the City speech Tuesday offered a snapshot of the looming leadership vacuum. There was Brown behind a lectern, on the landing of the graceful central stairway, while the supervisors sat below him like impish schoolboys (and they are virtually all boys: District elections, which were supposed to usher in new, progressive, representative city government, just happened to bring in 10 men, all but two of them white, and one black woman, Sophie Maxwell). Newsom sat quietly in the center -- he's the good schoolboy -- while to the mayor's left the impish Daly and Gonzalez whispered to one another and fidgeted, as Tom Ammiano sat beside them, smiling and making nice with everybody. Ammiano has tried to take the young left's revolt against him in stride. "Yeah, I'm angry, but I don't have time to be angry," he told me shortly after Gonzalez declared. "I get their impatience. I'm 61, they're all in their 30s. It's the father thing -- and I'm sure they always wanted a gay, queenie father." One of Ammiano's problems with appearing mayoral is that he's almost pathologically nice; no one fears him. But none of his rivals have gravitas, either; Gonzalez probably could, except he shuns such old-fashioned trappings of power.

And yet, for all of Brown's gravitas and power, he can't simply hand the reins of the city over to Newsom. He hasn't even been able to unite the storied Brown-Burton machine behind his candidate -- his longtime friend, State Sen. John Burton, is backing Alioto, and so is his buddy Joe O'Donohue from the powerful Residential Builders' Association. Even though Brown endorsed Newsom, you get the feeling that he doesn't entirely trust him. Plus the mayor's got a mischievous streak himself and he can't help messing with young Gavin. When Gonzalez entered the race he quipped that he "made Gavin look stiffer," which was projected on a wall during the Gonzalez kickoff party in September. Brown is not known for false modesty, but the last time we talked, when I suggested he ought to be able to bring Burton and O'Donohue on board for Newsom, he told me he simply couldn't. "There's an observation of Gavin as being unreliable. So I can't go to Joe O'Donohue or John Burton and say, you can't do this. They have too many examples of unreliability."

What some call "unreliability," of course, others call independence, and there's a way that Brown's occasional public distancing may help Newsom, in a town where the mayor is a polarizing figure, loved by many but hated by more than a few. Newsom has bucked Brown, who appointed him to the board in 1997 (he's since been reelected), on several key votes, and recently said he'd replace the mayor's choice for police chief. And despite the left's depiction of Newsom as the creation of evil, monolithic business leaders, business doesn't entirely trust him either. Financier, philanthropist and liberal Republican Warren Hellman is backing Leal. Newsom is a little bit too young and -- to his credit -- too much of a synthesizer and triangulator, in the Clinton mode, for any one group to monolithically back him. His decision to support a ballot measure increasing the local minimum wage, for instance, probably cost him some business support.

I've always sort of liked Newsom, liked his wonkiness. His campaign Web site reads like a think-tank site, with policy papers on every imaginable topic; last time we talked he was pushing his plan for a local Earned Income Tax Credit for San Francisco's working poor, an underappreciated New Democrat priority, even in the face of a budget deficit. When I was profiling Matt Gonzalez for San Francisco magazine, the Green Party leader kept needling me that I was giving him a hard time -- asking tough questions about his late decision to run -- because I have a dark political secret: I'm a Bernal Heights lefty who's soft on Ammiano (he lives blocks away and represents my district). I have a dark secret, all right: It's that I like Ammiano, but before Gonzalez joined the race, I was torn between him and Newsom (I still haven't gotten over Alioto's challenging Agnos in 1991, and Leal's campaign just never added up for me). I covered Newsom's "Care not Cash" initiative last year and found myself persuaded by some of its logic: It would have slashed the cash grant the city gives the homeless from roughly $350 to $59 -- all around San Francisco, other counties have done something similar, making us a magnet for general assistance recipients -- and put the money into housing and services, creating a $14 million revenue stream for supportive housing at a time of budget cutbacks.

But mostly I hated the campaign against Care Not Cash, which was really a campaign against Newsom, in which nasty lefty know-it-alls hit him with pies, threw stink bombs into the restaurants he owned, papered the town with fliers printing his home phone number and demonized him mostly because they could. It was a thuggish kind of politics that disgusts me, and I blamed its practitioners for marginalizing someone who isn't a villain, who doesn't have horns, who had been a champion of drug treatment and a smart mind and decent vote on human service issues, whose crime it was to see the problems of poverty and social services differently from the advocacy community.

Yet lately I've had to admit Newsom deserves some of the blame, too. His new initiative, Prop. M, which bans aggressive panhandling, seems to be an exercise in divisive politics. I met with Newsom shortly before he put it on the ballot, and it was one of those days you could see the angel and the devil on his shoulders, whispering in each ear. Some liberal supporters of Care Not Cash -- most notably Human Services chief Trent Rhorer, who helped write it -- were opposing the new measure, which would ban "aggressive panhandling" -- physical contact, verbal threats, following someone who says no -- plus add new limits: no begging at bus stops, on median strips, in parking lots. It also would take the city's most Draconian laws -- technically, begging is illegal in San Francisco -- off the books, which let Newsom pitch it as another hybrid, left-right solution. But nobody was buying it. "I think Gavin truly did Care Not Cash as a way to help people," Rhorer said in April. "But I worry that there's no way you can really say this measure will do that. I mean, call a spade a spade: If you want to make the streets cleaner for businesses and tourists, do it. But don't bill it as compassion."

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